@Alexander Felice said it better than I can "people make awful choices all the time, in the face of good advice" Call it the institution imperative, herd mentality, whatever you want. 

So I'm ready (mentally) to make my first multi family investment purchase, but what should I do first?

Take care of it quick and move forward; don't let it take a minute more of your mental space. 

If you have the mentality of a long term investor, then selling shouldn't really be a high criteria item (this is what I've been lead to believe).

The master leasing in my area is essentially having an agency be on the lease and they would be responsible for finding tenants, paying the rent, having an employee check the house, and tenants whom general can use the help such as victims of domestic violence, homelessness, mental health, etc.

After living here for 15 years, it's really a small city trapped in a large town mentality. 

If you come out ahead, and it saves you the mental / emotional strain there’s nothing wrong with pivoting to an area less at risk of flooding. 

I am always making mental notes about that stuff when I hear or read things.Do me a favor @Derrick Craig and give me a couple days then send me a message reminding me of this.  

Here is the hurdle that I'm mentally up against: While certain expenses are in actuality directly tied to your gross rental income (vacancy and property management) some expenses are not (maintenance and CapEx). 

A couple things to address:1) 2-4 unit non-owner occupied are 25% down and we just locked in a 4.13% but rates have ticked up a bit so I would use 4.5%2) You hear all over the place that you have to buy place based on current rents....Great....Highly unlikely you will be buying anything in the Seattle to Everett region with that mentality.